San Jose Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top San Jose Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton by Hilton Montevideo Carrasco

Hampton by Hilton Montevideo Carrasco

3.5 out of 5
Price was CA $1,885, price is now CA $1,768 per person
CA $1,768
per person
Nov 22 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Montevideo (MVD)
9.2/10 Wonderful! (805 reviews)
Check in was swift and very helpful and attentive staff.

Reviewed on Aug. 26, 2025

Hyatt Centric Montevideo

Hyatt Centric Montevideo

4.5 out of 5
Pocitos
Price was CA $2,742, price is now CA $2,361 per person
CA $2,361
per person
Nov 22 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Montevideo (MVD)
9.4/10 Exceptional! (824 reviews)
Property very nice, clean, well located, staff courteous but not particularly nice or gracious

Reviewed on Jul. 24, 2025

Regency Park Hotel

Regency Park Hotel

4 out of 5
Price was CA $2,212, price is now CA $1,873 per person
CA $1,873
per person
Oct 7 - Oct 13
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Montevideo (MVD)
8.8/10 Excellent! (223 reviews)
Tiene que continuar C la profesionalización del personal (son muy amables y respetuosos pero necesitan más entrenamiento El inmueble necesita una puesta al día (ej de noche no había agua caliente Pero la propiedad es hermosa ,

Reviewed on Aug. 25, 2025

Regency Way Montevideo Hotel

Regency Way Montevideo Hotel

3.5 out of 5
Pocitos
Price was CA $2,129, price is now CA $1,804 per person
CA $1,804
per person
Oct 7 - Oct 13
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Montevideo (MVD)
8.8/10 Excellent! (1,001 reviews)
Excellent customer service. I have stayed here before but this time Ana was the difference. She was very helpful and made sure everything was perfect and took care of everything. I needed some help with luggage, getting a taxi at 4:30am. She even made sure I had refreshments ready for my early departure to the airport. This is my new home away from home. Thanks Ana

Reviewed on Sep. 4, 2025

Regency Golf - Hotel Urbano

Regency Golf - Hotel Urbano

4 out of 5
Punta Carretas
Price was CA $2,219, price is now CA $1,893 per person
CA $1,893
per person
Oct 7 - Oct 13
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Montevideo (MVD)
8.6/10 Excellent! (872 reviews)
Hotel is located close to some good restaurants, shopping and rambla. They need to work in the cleanliness of the rooms. Red pillows were stained and dirty !! Light in room does not working. They need to work in the details !

Reviewed on Aug. 26, 2025

San Jose Hotel Deals

Dazzler by Wyndham Montevideo

Dazzler by Wyndham Montevideo

3.5 out of 5
21 de Setiembre 2752, Pocitos, Montevideo
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 7 to Sep 8
CA $135
CA $135 total
Sep 7 - Sep 8
includes taxes & fees
Dazzler by Wyndham Montevideo
Esplendor by Wyndham Montevideo Cervantes

Esplendor by Wyndham Montevideo Cervantes

4 out of 5
Soriano 868, Montevideo
The price is CA $106 per night from Sep 29 to Sep 30
CA $106
CA $106 total
Sep 29 - Sep 30
includes taxes & fees
Esplendor by Wyndham Montevideo Cervantes
Puerto Mercado Hotel

Puerto Mercado Hotel

3.5 out of 5
Cerrito 262, Montevideo
Fully refundableReserve now, pay when you stay
The price is CA $77 per night from Sep 18 to Sep 19
CA $77
CA $77 total
Sep 18 - Sep 19
includes taxes & fees
Puerto Mercado Hotel
See all 219 properties in San Jose
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a San Jose vacation package cost?
Tailor make your San Jose package from as little as CA $1,768. Pick from any combination of rental cars, flights and hotels to build the trip you've been dreaming about. Don't forget to add on one or two experiences!
How do I get a cheap travel package to San Jose?
Bundle your flights and hotels with Expedia to save big on your next trip. With more than 550 partner airlines and 1,000,000 hotels around the globe, your San Jose vacation package can be tailored exactly to suit your budget. With all that extra money, why not include one or more awesome tours and activities? It's an easy way to unlock even more savings. That dream vacation to San Jose is much closer than you thought!
How far in advance should I book my San Jose vacation?
Browse Expedia to compare international airfares as soon as possible. You can generally purchase a ticket up to a year in advance. If you don't see your preferred air carrier, or you've left things to the last moment, don't worry. Cheap tickets to San Jose sometimes occur within weeks of departure.
What does an Expedia San Jose travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to create your ideal San Jose travel package. Once you've made your booking, you can add on fun stuff like day tours and activities. Don't forget — the more you bundle, the more you'll save!
What should I know before booking a San Jose travel package?
A travel package can be customized for your circumstances and is a fantastic way to make your budget go further. What you include is completely up to you. Hotels, rental cars and flights — mix and match whatever combination works with your plans.
Can I choose my airline with a San Jose Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to choose. We have access to more than 550 airline partners all over the world, so you have lots of choice when creating your San Jose trip.
If I'm not able to travel, can I cancel my San Jose vacation package?
Because we know life can throw you a few curveballs, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it with no penalties. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

What to do in San Jose

Premium Day Trip to Montevideo from Buenos Aires

Private Full Day Trip to Montevideo from Buenos Aires

CA $1,308
per adult
Private Full Day Trip to Montevideo from Buenos Aires
2-Days and 1 Night in Montevideo from Buenos Aires

2-Days and 1 Night in Montevideo from Buenos Aires

CA $1,473
per traveller
2-Days and 1 Night in Montevideo from Buenos Aires
Private Castillo Viejo Winery Tour from Las Piedras

Private Castillo Viejo Winery Tour from Las Piedras

CA $125
per adult
Private Castillo Viejo Winery Tour from Las Piedras
See all activities in San Jose
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.